3-Vinylpyridine → 7-[(E)-2-pyridin-3-ylvinyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

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A mixture of bis(tri-t-butylphosphino)palladium (18.4 mg, 0.036 mmol; Strem), 3-vinylpyridine (123 mg, 0.52 mmol; TCI-US), sodium t-butoxide (87 mg, 0.90 mmol; Aldrich) and the product of Example 1B (105 mg, 0.36 mmol) was combined with 1,4-dioxane (2 mL). The mixture was purged with a stream of nitrogen for 2 minutes, then stirred at 85° C. in a sealed tube. After 18 hours, the reaction mixture was cooled to ambient temperature. Magnesium sulfate (43 mg, 0.36 mmol) and 3-vinylpyridine (85 mg, 0.36 mmol; TCI-US) were added and the reaction mixture was again purged with nitrogen, sealed and stirred at 100° C. for 24 hour in a sealed tube. The reaction mixture was cooled to ambient temperature, filtered through a glass microfiber frit, rinsed with methanol (2 mL) and purified by reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 30-100% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to afford the title compound: 1H NMR (400 MHz, methanol-d4) δ ppm 2.01-2.18 (m, 4 H), 3.02-3.12 (m, 2 H), 3.14 (pent, J=3.4 Hz, 1 H), 3.20-3.29 (m, 2 H), 4.23 (s, 2 H), 7.03 (t, J=7.6 Hz, 1 H), 7.25 (d, J=16.5 Hz, 1 H), 7.27 (d, J=7.3 Hz, 1 H), 7.41 (d, J=7.3 Hz, 1 H), 7.43 (dd, J=8.2, 4.9 Hz, 1 H), 7.74 (d, J=16.5 Hz, 1 H), 8.07-8.15 (m, 1 H), 8.38 (dd, J=4.6, 0.9 Hz, 1 H), 8.75 (d, J=1.5 Hz, 1H); MS (APCI) m/z 316 (M+H)+.

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